methyl 2,3,4,6-tetra-O-benzyl-α-D-erythro-D-gluco-octopyranoside | 1539282-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-benzyl-α-D-erythro-D-gluco-octopyranoside
• CAS: 1539282-45-5
• 化学式: C₃₇H₄₂O₈
• 分子量: 614.736
• InChiKey: IDRKUSSZSNYFRH-LGJXVWDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  95.84
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-α-D-erythro-D-gluco-octopyranoside 在 硫酸 、 乙酸酐 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 1,8-di-O-acetyl-2,3,4,6,7-penta-O-benzyl-β-D-erythro-D-gluco-octopyranoside 、 1,8-di-O-acetyl-2,3,4,6,7-penta-O-benzyl-α-D-erythro-D-gluco-octopyranoside
  参考文献：
  名称：

  In Vitro Characterization of LmbK and LmbO: Identification of GDP-d-erythro-α-d-gluco-octose as a Key Intermediate in Lincomycin A Biosynthesis

  摘要：

  Lincomycin A is a clinically useful antibiotic isolated from Streptomyces lincolnensis. It contains an unusual methylmercapto-substituted octose, methylthiolincosamide (MTL). While it has been demonstrated that the C-8 backbone of MTL moiety is derived from D-fructose 6-phosphate and D-ribose 5-phosphate via a transaldol reaction catalyzed by LmbR, the subsequent enzymatic transformations leading to the MTL moiety remain elusive. Here, we report the identification of GDP-D-etythro-alpha-D-gluco-octose (GDP-D-alpha-D-octose) as a key intermediate in the MTL biosynthetic pathway. Our data show that the octose 1,8-bisphosphate intermediate is first converted to octose 1-phosphate by a phosphatase, LmbK. The subsequent conversion of the octose 1-phosphate to GDP-D-alpha-D-octose is catalyzed by the octose 1-phosphate guanylyltransferase, LmbO. These results provide significant insight into the lincomycin biosynthetic pathway, because the activated octose likely serves as the acceptor for the installation of the C1 sulfur appendage of MTL.

  DOI：

  10.1021/ja412194w
• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-7,8-dideoxy-D-glycero-α-D-gluco-oct-7-enopyranoside 在 甲基磺酰胺 、 AD-mix-α 作用下， 以 水 、 叔丁醇 为溶剂， 以80%的产率得到methyl 2,3,4,6-tetra-O-benzyl-α-D-erythro-D-gluco-octopyranoside
  参考文献：
  名称：

  In Vitro Characterization of LmbK and LmbO: Identification of GDP-d-erythro-α-d-gluco-octose as a Key Intermediate in Lincomycin A Biosynthesis

  摘要：

  Lincomycin A is a clinically useful antibiotic isolated from Streptomyces lincolnensis. It contains an unusual methylmercapto-substituted octose, methylthiolincosamide (MTL). While it has been demonstrated that the C-8 backbone of MTL moiety is derived from D-fructose 6-phosphate and D-ribose 5-phosphate via a transaldol reaction catalyzed by LmbR, the subsequent enzymatic transformations leading to the MTL moiety remain elusive. Here, we report the identification of GDP-D-etythro-alpha-D-gluco-octose (GDP-D-alpha-D-octose) as a key intermediate in the MTL biosynthetic pathway. Our data show that the octose 1,8-bisphosphate intermediate is first converted to octose 1-phosphate by a phosphatase, LmbK. The subsequent conversion of the octose 1-phosphate to GDP-D-alpha-D-octose is catalyzed by the octose 1-phosphate guanylyltransferase, LmbO. These results provide significant insight into the lincomycin biosynthetic pathway, because the activated octose likely serves as the acceptor for the installation of the C1 sulfur appendage of MTL.

  DOI：

  10.1021/ja412194w